We describe the synthesis
of a new class of trisulfonamide calix[6]arene-based
wheels that can bind dialkylviologen salts, in apolar media. The threading
process occurs through a selective ion-pair recognition, established
by the sulfonamide groups with the counterions of the bipyridinium
salts, that dictates a conformational rearrangement of the corresponding
pseudorotaxanes.
We report a Michael addition of indoles to nitroalkene derivatives enabled by hydrogen-bonding interactions between trisulfonamide (TSA) calix[6]arene catalysts and protic solvents.
Understanding the role played by the nature, number, and arrangement of binding sites anchored to a macrocycle remains a topic of current interest for the synthesis of new interwoven species. We report the synthesis and detailed structural characterization of a new calix[6]arene derivative decorated with two phenylureido groups anchored at the diametrical position of the calix upper rim that adopts a 1,2,3‐alternate conformation in solution and in the solid state. Preliminary data on the ability of this host to form redox‐active pseudorotaxanes and rotaxanes are reported.
Operating molecular machines are based on switchable systems whose components can be set in motion in a controllable fashion. The presence of nonsymmetrical elements is a mandatory requirement to obtain and demonstrate the unidirectionality of motion. Calixarene-based macrocycles have proved to be very efficient hosts in the design of oriented rotaxanes and of pseudorotaxanes with strict control over the direction of complexation. A series of two-station rotaxanes based on bipyridinium-ammonium axles was synthesized and characterized. A recently reported supramolecularly assisted strategy for the synthesis of different orientational isomers was exploited, and the ammonium unit was identified as a proper secondary station for the calixarene. Displacement of the macrocycle was triggered by electrochemical reduction of the bipyridinium primary station, and it was shown that the shuttling is influenced both by the length of the chain of the axle component and by the position of the secondary station with respect to the calixarene rims.
A self-complexing lasso-like molecule has been synthesised as the first example of a calix[6]arene-based [1]pseudorotaxane. This artificial molecular lasso can be switched between self-threaded and dethreaded structures by redox stimulation.
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